Will I lose any of my settings, contacts, calendars, etc?

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All of your contacts, calendars items, and emails (including folders and folder structure) will be migrated to the new email system for you. The only thing it will not migrate for you are your email rules, Microsoft doesn’t give us the ability to move these for you. If you are using email rules and would like to continue, please click on this link for directions on how to save your rules and how to import them following migration.